2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-ethyl-7-fluoroquinoxalin-2(1H)-one

HRID 75383

Reaktionsgleichung

Reaktionsgleichung von HRID 75383
[CH2:1]([CH:3]1[NH:12][C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:14])[CH3:2].O1CCOCC1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C([O-])(O)=O.[Na+].O>[CH2:1]([C:3]1[C:4](=[O:14])[NH:5][C:6]2[C:11]([N:12]=1)=[CH:10][CH:9]=[C:8]([F:13])[CH:7]=2)[CH3:2]

Komponenten

6

Edukt 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 312751,4-DioxaneHCID 776236013-ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one

Produkt 1

HCID 672892053-ethyl-7-fluoroquinoxalin-2(1H)-oneAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel2×

Versuchsvorschrift

To a homogeneous solution of 3-ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one (60.61 g, 312.1 mmol) and 1,4-dioxane (1350 ml) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (75.91 g, 327.7 mmol) and the mixture was stirred using an overhead stirrer at rt for 2.5 h. At this time, the mixture was concentrated under reduced pressure to give a brown residue. The brown residue was suspended in saturated aqueous NaHCO3 (2 L), stirred for 30 min, filtered, washed with saturated aqueous NaHCO3 (1 L) to give a light green solid. The light green solid was re-suspended in saturated aqueous NaHCO3 (500 mL), well mixed, filtered, and washed with saturated aqueous NaHCO3 (500 mL) to give an off-white solid. The off-white solid was suspended in water (500 mL), well mixed, filtered, washed with water (1 L), air-dried overnight, and dried under high vacuum at 22° C. for 2 h to give 3-ethyl-7-fluoroquinoxalin-2(1H)-one (56.87 g, 94.8% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.36 (br. S, 1H), 7.76 (dd, J=9.0, 5.9 Hz, 1H), 7.11 (td, J=8.8, 2.7 Hz, 1H), 7.00 (dd, J=9.6, 2.7 Hz, 1H), 2.78 (q, J=7.4 Hz, 2H), 1.20 (t, J=7.4 Hz, 3H) Mass Spectrum (ESI) m/e=193.0 (M+1).

Aufarbeitung

  1. customat rt
  2. customfor 2.5 h
  3. concentrationAt this time, the mixture was concentrated under reduced pressure
  4. customto give a brown residue
  5. stirringstirred for 30 min
  6. filtrationfiltered
  7. washwashed with saturated aqueous NaHCO3 (1 L)
  8. customto give a light green solid
  9. additionwell mixed
  10. filtrationfiltered
  11. washwashed with saturated aqueous NaHCO3 (500 mL)
  12. customto give an off-white solid
  13. additionwell mixed
  14. filtrationfiltered
  15. washwashed with water (1 L)
  16. customair-dried overnight
  17. customdried under high vacuum at 22° C. for 2 h

Quellen und Nachweise

ORD-Eintrag
ord-51e43186795f4c46b32665ec70c1ad62
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835432B2

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